Ethyl Acetate → 7-Iodo-2-(3-phenyl-butyl)-2,3-dihydro-isoindol-1-one

HRID 2427632Notes

Reaction equation

CO[C:3](=[O:13])[C:4]1[C:9]([I:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.[C:14]1([CH:20]([CH3:24])[CH2:21][CH2:22][NH2:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[I:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:13])[N:23]([CH2:22][CH2:21][CH:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:24])[CH2:11]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.178 g, 0.5 mmol), 3-phenyl-butylamine (0.090 g, 0.6 mmol), and K2CO3 (0.166 g, 1.2 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-iodo-2-(3-phenyl-butyl)-2,3-dihydro-isoindol-1-one (0.046 g, 23%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.32 (d, 3H), 1.96 (m, 2H), 2.78 (m, 1H), 3.54 (m, 2H) 4.16 (s, 2H), 7.14-7.38 (m, 7H), 7.88 (d, 1H). GC-MS: m/z 391 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-db140141130846dcb7903422136804b3
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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